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Uchiha Itachi

Looks:Despite his status as an infamous shinobi, Itachi's appearance was not the most intimidating, apart from the intensity of his gaze. While living in Konoha, he would regularly have a gentle look in his eyes, especially directed towards his younger brother. After joining Akatsuki, they would regularly have a stern look to them.

Itachi was a young man with onyx eyes, black hair with bangs that framed his face, and a low-tied ponytail which reached down into his upper back. The ponytail was, however, later obscured by the high collar of the Akatsuki cloak he wore after joining the organisation. Itachi's most distinguishing features were the long, pronounced tear-troughs under his eyes. Itachi and Sasuke also bear slight similarities to one another in terms of their appearance as Naruto nearly mistook Itachi for Sasuke when they first met, while Tobi commented upon their resemblance when he first encountered Sasuke.

When he lived in Konoha, his casual clothes consisted of a black shirt with the Uchiha clan symbol on the back, and pants with a weapons pouch strapped to his back. When on duty, he would wear the standard ANBU uniform complete with arm guards, a flak jacket, and a porcelain mask which was fashioned to resemble a weasel with a dark, triangular marking on top. As a member of Akatsuki, he wore a slashed Konoha forehead protector and the standard Akatsuki cloak.

After his cloak was incinerated by Sasuke's Kirin during their fight in Part II, it was revealed that he wore similar clothes to that of the rest of Akatsuki. His attire consisted of a body mesh under a blue v-neck T-shirt with a sash around the waist, and blue pants. Like most members of Akatsuki, he wore the forehead protector of his home village with a horizontal line gouged through it to symbolise his broken ties with the village.

Personality: Ever since his first appearance, Itachi had always been inscrutable. Flashbacks showed that he used to be a compassionate brother, but his initial appearances depicted him as an Akatsuki criminal interested in the organisation's success and secrecy before all else. Later his interest in Akatsuki was revealed to be an act, and his true intentions for joining the organisation were to spy on it from within. Nonetheless, Itachi and his partner, Kisame, cooperated better than most Akatsuki partners, and despite the differences in personalities, appeared to have mutual respect for one another.

While a member of Akatsuki, Itachi possessed incredible control of his emotions, only showing surprise when opponents proved more powerful than expected, and even then did not lose his composure.

Itachi was shown to be highly intelligent: something even Tobi acknowledged. He was sharp, observant, and intuitive, being rarely caught off guard or deceived. Itachi had great foresight; his foreknowledge of Sasuke's victory against Deidara, his own pre-meditated death by Sasuke's hand, and the implantation of the Kotoamatsukami-imbued crow inside Naruto were some examples seen.

However, while Itachi was a powerful shinobi, he was not arrogant, and complimented his opponents at times on their abilities. After his death, Itachi realised that he should not have tried to deal with Sasuke on his own and encouraged Naruto to never forget his friends. Likewise, Itachi took no enjoyment in violence or combat, instead preferring to avoid battle or, if not possible, end it as quickly as he could.

Background Info.History: Itachi was born into the Uchiha clan as the eldest son of Mikoto and Fugaku Uchiha, and was praised by all as the best of his generation, and a genius above all others, even by the standards of the battle-adept Uchiha clan, Itachi's prowess far outshone their own. However, few could understand him. When he was only four, Itachi had already witnessed countless lives lost due to the Third Shinobi World War, which emotionally traumatised him and turned him into a pacifist.

Itachi was a highly perceptive child, wise beyond his years and spent much of his time researching the history of the village from the writings their ancestors left behind. Because of this, Itachi was never limited to the view of his own clan but worried about the fate of the village as a whole.

During the Nine-Tails' attack on Konoha, Itachi was left alone to take care of his infant brother Sasuke and promised to protect him no matter what. In the anime, it was shown that during their childhood, Itachi made a game of collecting paw prints of cats with his brother. The last paw print to be collected was Nekomata's, who Itachi had defeated and asked him to fight Sasuke with all his might when Sasuke got older.

At age 7, Itachi graduated from the Academy at the top of his class after only one year, mastered the Sharingan at age 8, passed the Chūnin Exams at age 10, enrolled in ANBU half a year later and became captain by 13. At some point in time in their childhood, Sasuke helped Itachi on one of his missions to capture a giant boar. Itachi told Sasuke to avoid his vital points. He then threw kunai with explosive tags around the boar, to confuse it and to give Sasuke an opportunity to shoot the boar. Sasuke, however, missed completely. After Sasuke apologised, Itachi told him he needs to train more.

Itachi was praised highly by his father, who saw the family's future in Itachi and hence inadvertently neglected his younger son. However, during this time Itachi showed great affection towards his little brother and even encouraged his father to come to the Academy enrolment ceremony for Sasuke, something their father had otherwise forgotten, caught up an important mission that would establish Itachi a place in the ANBU ranks.

When the Uchiha clan began planning to overthrow Konoha, Itachi, as an ANBU, was tasked with spying on the village. Knowing that a coup d'état would only escalate to the beginning of another ninja-world war, Itachi began spying on the Uchiha instead, passing on information to the Third Hokage and Konoha elders. Though the Third Hokage ultimately decided to reason with the Uchiha in order to dissuade them from their actions, Danzō Shimura met secretly with Itachi Uchiha and inveigled him into choosing the lives of his clansmen or that of his little brother. During this time he began to act strangely, not attending the clan meetings, speaking out against the clan, and becoming the prime suspect for the murder of his best friend Shisui Uchiha, who was drowned in the Naka River. In reality, Shisui died after he entrusted his left eye to Itachi, the other having been taken by Danzō. Due to this the clan lost hope in Itachi, and his father began shifting his focus to Sasuke instead. Meanwhile, the Third's attempts to negotiate a bloodless end to hostilities between the two parties were proving ineffective, so against Hiruzen's wishes, Danzō Shimura and the Konoha Council ordered Itachi to wipe out the Uchiha clan.

Before the fateful night arrived, Itachi discovered the existence of Tobi — under the guise of a vengeful Madara Uchiha — who was attempting to rekindle the flames of war in Konoha. In return for not attacking Konoha, Itachi offered to help him claim vengeance against the Uchiha for turning their backs on him decades earlier to which Tobi agreed. Itachi slaughtered his entire clan overnight, including his friends, superiors, family, and lover; prior to killing his parents, the two people whom he was most hesitant to kill, they stated that they were still proud of their eldest son, and requested that he took care of Sasuke before allowing a tearful Itachi to kill them. When Sasuke returned late from a training session, Itachi spared Sasuke because he loved his little brother, and as per the agreement between him and Danzō, did not want to take the life of the person most important to him. He lied to his brother, making himself out as a villain who had killed their innocent family only to test his capacity, and told Sasuke he was not even worth killing. In addition, Itachi told him, "You've always wanted to surpass me. That's why I'm going to let you live… if you wish to kill me, then hate me, despise me… and by all means flee, cling to your wretched life". Itachi also revealed to Sasuke the secret meeting place of the Uchiha, where Sasuke can learn the true history and purpose of the Sharingan. Itachi told him that in order to awaken the Mangekyō Sharingan, Sasuke had to kill the person closest to him, and that when they met again, they should have the same eyes.

Sasuke managed to stand back up, awaken his Sharingan, and pursue Itachi. Upon reaching Itachi, he managed to knock off his forehead protector. Itachi shed a tear as he was picking up his forehead protector, then proceeded to incapacitate Sasuke, who awoke in the hospital, only remembering up to Itachi's speech. By doing all this, Itachi hoped Sasuke would take vengeance on him and become a hero to Konoha, thus redeeming the Uchiha name. Hoping that his little brother would someday be powerful enough to kill him, Itachi left the village as a traitor. Knowing that Konoha would still want to eliminate Sasuke, Itachi pleaded with the Third Hokage to keep Sasuke safe and threatened Danzō not to harm Sasuke or else he would reveal everything he knew about Konoha's secrets to enemy nations.

Itachi joined Akatsuki in order to keep an eye on the organisation, along with Tobi, in case either ever acted against Konoha, all the while planning for his death at Sasuke's hands. During his time in Akatsuki, Orochimaru tried to steal his body to gain the Sharingan, but Itachi trapped him in a genjutsu and severed his left hand. Itachi was further partnered with Kisame Hoshigaki, who initially tried to intimidate him. However, they eventually became good partners. Sometime after Orochimaru fled, Itachi helped recruit Deidara by beating him in battle using only genjutsu, to which Deidara swore vengeance.

At some point in time, Itachi contracted a fatal disease. He kept himself alive through the intake of various medicines, and sheer "willpower", in the hopes of living long enough to die by Sasuke's hands.